Cottage holiday rentals in Mathews County

Beach Music Chesapeake Bay Getaway for all Seasons

This unique cottage has a sophisticated style all its own! Newly built on the original footprint, it has the advantage of capturing outdoor beauty within! Walk to a private beach within minutes! Lie out on a private beach for this small community, take a walk to an historical lighthouse along a pristine beach untouched by civilization, wade into the Chesapeake Bay or Mobjack Bay and enjoy a swim, jet ski, float, boat, fish, paddle board or even windsurf! Just as beautiful in Fall and Winter!

320 Water View and Access Retreat - Fiddlers Green

Fiddler's Green is a peaceful retreat with 2 BR+ Loft (2nd LR), 2 Ba. This getaway on the water features wraparound decks and views of the Chesapeake Bay, Piankatank River, and Kibble Pond. This has been a well loved place our family has enjoyed for over two decades. From high open spaces, to easy water access off NEW private dock for summer activities on the water. Relax in the hammock, set up the fire pit, pull out lounge chairs, or rock on the deck overlooking the water. The choice is yours.

The Nook; Peaceful 2 bedroom cottage by the bay

Relax or go-for-it! The Nook is a stylish cozy cottage with great indoor/outdoor space. With water view and access including pier and boat ramp enjoy your coffee on the deck before taking to the water in one of the two kayaks or canoe or enjoying a bike ride (4 available) to get up close with nature. Catch fish, crabs or just a sunburn while enjoying time on the water. When ready there's plenty of shopping, eating and beaching to do in nearby towns! All topped off with a sunset over the water!

Old Log Cabin School House w/10 acres on the Bay

Bring your family and relax in this Log Cabin School, hand built in 1899. Situated on a private peninsula, and with over 10 acres you will have unbelievable views and access to everything nature has to offer on both land and water! With its own private dock and beach, you will be equipped with kayaks, canoes, fishing rods, and crab traps to spend the day adventuring the Chesapeake Bay. Or you can sit back and relax on one of many water side hammocks, or just enjoy a fire on the private beach.

Sunset Haven

Enjoy the Island life in this newly renovated, cheerful 3 bedroom, 2 bathroom cottage with 3 porches with water & sunset views. This charming 1900’s farmhouse is situated on historic Gwynns Island in Mathews County, a waterman’s delight. Small town with locally owned shoppes and restaurants is less than 10 minutes away. Public boat landing is less than 2 miles away on the island at the Hole In The Wall Restaurant. Bring your paddle boards, kayaks, & boat! This is a non-smoking property.

3 BR Bay Home w Private Dock & all the Amenities

Half Shell Haven: an escape to the land and sea perfectly outfitted for enjoying the fruits of both, in what we like to call "low country" Virginia. The Haven is a beautifully maintained, open concept home with 3 bds and 2 baths that can comfortably sleep 8. A full kitchen and dining area (in- and outdoors) are at your disposal for enjoying the local bounty with friends and family. The backyard includes a game shed (with bar!), a hot tub and a private dock for crabbing or kayaking, or both.

Blue Moon Haven- Cozy Vintage Cottage in Mathews

Escape to this charming 1930s cottage nestled on a serene 1-acre property in Moon, Virginia. Just minutes from the Chesapeake Bay, it’s perfect for nature lovers and weekend adventurers. Wake up to the soothing sounds of birds, enjoy morning strolls under the trees, or embark on an afternoon kayaking trip. Relax on the large screened-in porch, free from bugs. Only 3 miles from the quaint town of Mathews and Colonial Williamsburg is just an hour’s drive away. Your ideal getaway awaits!

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

The Cottage @ Captain Genes - Secluded Waterfront

Get away from the crowds! Private, secluded upscale waterfront cottage on ~5 acres; pool/hot tub feet from the back door (hot tub open year round). Waterview from most rooms. Direct Chesapeake Bay access on property via dock / kayak launch. ~15 mins to downtown. Fish/crab, kayak, screened porch views, relax by the pool, fire pit or hot tub with a drink. Bring your boat - marina ~4 mi away - put-in there & tie-up at our pier!

Waterfront w/Floating Dock, Kayaks~Family Home

Cove Place is a newly renovated, 1 -story home with a dock and boat/trailer parking on 4 secluded acres. There is a smart tv in every room including the screened porch. Close to Zoll Vineyards (4.1 miles away), a chef owned winery that focuses on food and beverage pairings in their tasting room and Under the Stars Farm (8.6 miles), a family owned and operated lavender farm.

Bavon Beach HideAway Cottage

Enjoy a charming cottage in a private community with direct access to a powdery white sand beach on Chesapeake Bay. Perfect for kayaking, fishing, biking, beach walks, and watching stunning sunrises. Cozy and inviting, ideal for relaxing extended stays of 30+ days. Unwind, explore, and savor the peaceful beauty of the bay—your perfect retreat awaits!

Little Gray Beach House

Gwynn's Island cottage with magnificent views of the Chesapeake Bay! Located between 2 white sandy beaches--perfect for swimming or fishing. Great spot for kayaking and/or biking around historic island. Spectacular sunrises! Great bayside deck for cookouts, bird watching, and frequent dolphin-spotting!